JP2007505873A5 - - Google Patents
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- JP2007505873A5 JP2007505873A5 JP2006526684A JP2006526684A JP2007505873A5 JP 2007505873 A5 JP2007505873 A5 JP 2007505873A5 JP 2006526684 A JP2006526684 A JP 2006526684A JP 2006526684 A JP2006526684 A JP 2006526684A JP 2007505873 A5 JP2007505873 A5 JP 2007505873A5
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- JP
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- Prior art keywords
- alkyl
- formula
- group
- oxy
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000217 alkyl group Chemical group 0.000 claims 133
- 150000003246 quinazolines Chemical class 0.000 claims 45
- -1 hydroxy, cyano, amino, carboxy, carbamoyl Chemical group 0.000 claims 41
- 125000003545 alkoxy group Chemical group 0.000 claims 37
- 125000001424 substituent group Chemical group 0.000 claims 32
- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 239000001257 hydrogen Substances 0.000 claims 30
- 229910052757 nitrogen Inorganic materials 0.000 claims 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
- 125000003282 alkyl amino group Chemical group 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 16
- 125000000524 functional group Chemical group 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000005236 alkanoylamino group Chemical group 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 8
- 125000001589 carboacyl group Chemical group 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 125000004423 acyloxy group Chemical group 0.000 claims 7
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 6
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 238000003780 insertion Methods 0.000 claims 4
- 230000037431 insertion Effects 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 3
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims 2
- 230000001028 anti-proliverative effect Effects 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims 2
- PGHNHXUHPOOBFU-QFIPXVFZSA-N 1-[(2s)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxymethyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@H]1COC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 PGHNHXUHPOOBFU-QFIPXVFZSA-N 0.000 claims 1
- DBTFQRQGEVHZRH-FQEVSTJZSA-N 1-[(2s)-2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxymethyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCC[C@H]1COC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 DBTFQRQGEVHZRH-FQEVSTJZSA-N 0.000 claims 1
- OBYKUWKNPXQDFJ-QHCPKHFHSA-N 1-[(3s)-3-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1N(C(=O)CN(C)C)CCC[C@@H]1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 OBYKUWKNPXQDFJ-QHCPKHFHSA-N 0.000 claims 1
- LTPJXGTYIXMFCA-NRFANRHFSA-N 1-[(3s)-3-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-hydroxyethanone Chemical compound C1N(C(=O)CO)CCC[C@@H]1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 LTPJXGTYIXMFCA-NRFANRHFSA-N 0.000 claims 1
- MTILJCKKYKSSDN-FQEVSTJZSA-N 1-[(3s)-3-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypyrrolidin-1-yl]-2-hydroxyethanone Chemical compound C1N(C(=O)CO)CC[C@@H]1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 MTILJCKKYKSSDN-FQEVSTJZSA-N 0.000 claims 1
- JGVZYQZWYSNTCH-UHFFFAOYSA-N 1-[3-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxyazetidin-1-yl]-2-hydroxyethanone Chemical compound C1N(C(=O)CO)CC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 JGVZYQZWYSNTCH-UHFFFAOYSA-N 0.000 claims 1
- CZSCWJRJMFZFKN-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 CZSCWJRJMFZFKN-UHFFFAOYSA-N 0.000 claims 1
- WGQGZSZZIHOYIG-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(C)=O)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CN=CC=N1 WGQGZSZZIHOYIG-UHFFFAOYSA-N 0.000 claims 1
- HHNVLCSQZBHLNB-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)C2=C1 HHNVLCSQZBHLNB-UHFFFAOYSA-N 0.000 claims 1
- WGXUEMXKOANYOP-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)C2=C1 WGXUEMXKOANYOP-UHFFFAOYSA-N 0.000 claims 1
- REHCWAJWIQRJSL-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)C2=C1 REHCWAJWIQRJSL-UHFFFAOYSA-N 0.000 claims 1
- YXDCDWQQOISSGA-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 YXDCDWQQOISSGA-UHFFFAOYSA-N 0.000 claims 1
- PWYDEQIFZMVYET-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-2-hydroxyethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CO)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 PWYDEQIFZMVYET-UHFFFAOYSA-N 0.000 claims 1
- DLTYTEJYAVHQND-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(C)=O)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 DLTYTEJYAVHQND-UHFFFAOYSA-N 0.000 claims 1
- ZTLIKJIKMQGZPP-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 ZTLIKJIKMQGZPP-UHFFFAOYSA-N 0.000 claims 1
- CONRNKRWLJGEOF-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 CONRNKRWLJGEOF-UHFFFAOYSA-N 0.000 claims 1
- TVTCNDDTASWGPG-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 TVTCNDDTASWGPG-UHFFFAOYSA-N 0.000 claims 1
- DTJKKDWPYCFBJL-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical class C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 DTJKKDWPYCFBJL-UHFFFAOYSA-N 0.000 claims 1
- HZXMBZJCQBUOES-UHFFFAOYSA-N 1-[4-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]quinazolin-6-yl]oxypiperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 HZXMBZJCQBUOES-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- ZASCFESQWRTKCG-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[3-methoxy-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2N=CC=NC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(C(=O)CN(C)C)CC1 ZASCFESQWRTKCG-UHFFFAOYSA-N 0.000 claims 1
- UPBAVUPJRVMCCR-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[3-methoxy-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(C(=O)CN(C)C)CC1 UPBAVUPJRVMCCR-UHFFFAOYSA-N 0.000 claims 1
- GWVYGWZSKXFUDP-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=CC(OCC=4N=CC=NC=4)=CC=3)C2=C1 GWVYGWZSKXFUDP-UHFFFAOYSA-N 0.000 claims 1
- UVCJJKZUWSAMAE-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=CC(OCC=4N=CC=CC=4)=CC=3)C2=C1 UVCJJKZUWSAMAE-UHFFFAOYSA-N 0.000 claims 1
- NKHXKUSZNCCXTE-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-[(3-fluorophenyl)methoxy]-3-methoxyanilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical class C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC(OC)=C2OC1CCN(C(=O)CN(C)C)CC1 NKHXKUSZNCCXTE-UHFFFAOYSA-N 0.000 claims 1
- HFHOERMVRHCGBS-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-[(3-fluorophenyl)methoxy]-3-methoxyanilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(C(=O)CN(C)C)CC1 HFHOERMVRHCGBS-UHFFFAOYSA-N 0.000 claims 1
- JSVRRJAUFUTRCW-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-[(3-fluorophenyl)methoxy]anilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 JSVRRJAUFUTRCW-UHFFFAOYSA-N 0.000 claims 1
- YOQLVJQTNWDMPQ-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-[4-[(3-fluorophenyl)methoxy]anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1OC1=CC=C(N=CN=C2NC=3C=CC(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 YOQLVJQTNWDMPQ-UHFFFAOYSA-N 0.000 claims 1
- RPDPJGBITDCLOA-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[7-methoxy-4-[3-methoxy-4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2N=CC=NC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC(OC)=C2OC1CCN(C(=O)CN(C)C)CC1 RPDPJGBITDCLOA-UHFFFAOYSA-N 0.000 claims 1
- CRWGJNQMNWADKW-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[7-methoxy-4-[3-methoxy-4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC(OC)=C2OC1CCN(C(=O)CN(C)C)CC1 CRWGJNQMNWADKW-UHFFFAOYSA-N 0.000 claims 1
- DNRBJKZGVVZPSC-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[7-methoxy-4-[4-(pyrazin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1)=CC=C1OCC1=CN=CC=N1 DNRBJKZGVVZPSC-UHFFFAOYSA-N 0.000 claims 1
- JFIBRFHGXARFDL-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[7-methoxy-4-[4-(pyridin-2-ylmethoxy)anilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)CN(C)C)C(OC)=CC2=NC=NC=1NC(C=C1)=CC=C1OCC1=CC=CC=N1 JFIBRFHGXARFDL-UHFFFAOYSA-N 0.000 claims 1
- ALDKMUMLEZDDDX-UHFFFAOYSA-N 2-hydroxy-1-[3-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-6-yl]oxyazetidin-1-yl]ethanone Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC(C1=C2)=NC=NC1=CC=C2OC1CN(C(=O)CO)C1 ALDKMUMLEZDDDX-UHFFFAOYSA-N 0.000 claims 1
- WGVIMYSLSFIRNA-UHFFFAOYSA-N 2-hydroxy-1-[4-[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]quinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(C(=O)CO)CC1 WGVIMYSLSFIRNA-UHFFFAOYSA-N 0.000 claims 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- GVTKSUVXHBZNTA-UHFFFAOYSA-N 6-(1-methylsulfonylpiperidin-4-yl)oxy-n-[4-(1,3-thiazol-2-ylsulfanyl)phenyl]quinazolin-4-amine Chemical compound C1CN(S(=O)(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=CC(SC=4SC=CN=4)=CC=3)C2=C1 GVTKSUVXHBZNTA-UHFFFAOYSA-N 0.000 claims 1
- FHQTVYVBVMWTPS-UHFFFAOYSA-N 7-methoxy-6-(1-methylsulfonylpiperidin-4-yl)oxy-n-[4-(1,3-thiazol-2-ylsulfanyl)phenyl]quinazolin-4-amine Chemical compound C=12C=C(OC3CCN(CC3)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC(C=C1)=CC=C1SC1=NC=CS1 FHQTVYVBVMWTPS-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 241000282412 Homo Species 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- FHVDJQINBGRTEQ-UHFFFAOYSA-N n-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylphenyl]-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical class CN1C=CN=C1SC(C(=C1)Cl)=CC=C1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(S(C)(=O)=O)CC1 FHVDJQINBGRTEQ-UHFFFAOYSA-N 0.000 claims 1
- BAGWNVXNHRKDRU-UHFFFAOYSA-N n-[3-chloro-4-(pyrazin-2-ylmethoxy)phenyl]-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C1CN(S(=O)(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=NC=4)=CC=3)C2=C1 BAGWNVXNHRKDRU-UHFFFAOYSA-N 0.000 claims 1
- XUTCVYQECWOYIA-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C1CN(S(=O)(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 XUTCVYQECWOYIA-UHFFFAOYSA-N 0.000 claims 1
- GTAPRRNJTXVVRK-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-6-[(1-methylsulfonylpyrrolidin-3-yl)methoxy]quinazolin-4-amine Chemical compound C1N(S(=O)(=O)C)CCC1COC1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)C2=C1 GTAPRRNJTXVVRK-UHFFFAOYSA-N 0.000 claims 1
- IIOUGCSKSQIEQD-UHFFFAOYSA-N n-[3-ethynyl-4-[(3-fluorophenyl)methoxy]phenyl]-7-methoxy-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(CC3)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC(C=C1C#C)=CC=C1OCC1=CC=CC(F)=C1 IIOUGCSKSQIEQD-UHFFFAOYSA-N 0.000 claims 1
- MQIAKRLIMWVTPK-UHFFFAOYSA-N n-[3-fluoro-4-(1-methylimidazol-2-yl)sulfanylphenyl]-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical class CN1C=CN=C1SC(C(=C1)F)=CC=C1NC(C1=C2)=NC=NC1=CC=C2OC1CCN(S(C)(=O)=O)CC1 MQIAKRLIMWVTPK-UHFFFAOYSA-N 0.000 claims 1
- QWVDAJRPQDDAEF-UHFFFAOYSA-N n-[3-fluoro-4-(1-methylimidazol-2-yl)sulfanylphenyl]-7-methoxy-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(CC3)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC(C=C1F)=CC=C1SC1=NC=CN1C QWVDAJRPQDDAEF-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
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| EP03292279 | 2003-09-16 | ||
| PCT/GB2004/003931 WO2005026151A1 (en) | 2003-09-16 | 2004-09-14 | Quinazoline derivatives as tyrosine kinase inhibitors |
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| JP (1) | JP2007505873A (enExample) |
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| AU (1) | AU2004272350A1 (enExample) |
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| IL (1) | IL174258A0 (enExample) |
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| NO (1) | NO20061321L (enExample) |
| WO (1) | WO2005026151A1 (enExample) |
| ZA (1) | ZA200602190B (enExample) |
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| JP2005515176A (ja) * | 2001-11-03 | 2005-05-26 | アストラゼネカ アクチボラグ | 抗腫瘍剤としてのキナゾリン誘導体 |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| US6924285B2 (en) | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| US20070032513A1 (en) * | 2003-09-16 | 2007-02-08 | Hennequin Laurent F A | Quinazoline derivatives |
| DK1667991T3 (da) * | 2003-09-16 | 2008-08-18 | Astrazeneca Ab | Quinazolinderivater som tyrosinkinaseinhibitorer |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| CA2541100A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazenca Ab | Quinazoline derivatives |
| CN1882570B (zh) * | 2003-09-19 | 2010-12-08 | 阿斯利康(瑞典)有限公司 | 喹唑啉衍生物 |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| ATE413389T1 (de) | 2004-02-03 | 2008-11-15 | Astrazeneca Ab | Chinazolinderivate |
| US20070232607A1 (en) * | 2004-06-04 | 2007-10-04 | Bradbury Robert H | Quinazoline Derivatives as Erbb Receptor Tyrosine kinases |
| US7947676B2 (en) * | 2004-12-14 | 2011-05-24 | Astrazeneca Ab | Pyrazolo[3,4-d]pyrimidine compounds as antitumor agents |
| GB0504474D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| GB0508715D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| WO2007003486A1 (de) * | 2005-07-04 | 2007-01-11 | Boehringer Ingelheim International Gmbh | Verfahren zur herstellung von chinazolinonderivaten |
| EP1919900A2 (de) * | 2005-08-22 | 2008-05-14 | Boehringer Ingelheim International Gmbh | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| WO2007034143A1 (en) * | 2005-09-20 | 2007-03-29 | Astrazeneca Ab | Quinazoline derivatives as anticancer agents |
| US7820683B2 (en) * | 2005-09-20 | 2010-10-26 | Astrazeneca Ab | 4-(1H-indazol-5-yl-amino)-quinazoline compounds as erbB receptor tyrosine kinase inhibitors for the treatment of cancer |
| CA2755268C (en) | 2005-11-15 | 2013-12-31 | Array Biopharma, Inc. | Erbb inhibitors |
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| EP1921070A1 (de) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| WO2008095847A1 (de) | 2007-02-06 | 2008-08-14 | Boehringer Ingelheim International Gmbh | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| TWI377944B (en) * | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
| US8497369B2 (en) | 2008-02-07 | 2013-07-30 | Boehringer Ingelheim International Gmbh | Spirocyclic heterocycles medicaments containing said compounds, use thereof and method for their production |
| NZ589883A (en) | 2008-05-13 | 2012-06-29 | Astrazeneca Ab | Fumarate salt of 4- (3-chloro-2-fluoroanilino) -7-methoxy-6- { [1- (n-methylcarbamoylmethyl) piperidin- 4-yl] oxy} quinazoline |
| EP2313397B1 (de) | 2008-08-08 | 2016-04-20 | Boehringer Ingelheim International GmbH | Cyclohexyloxy-substituierte heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| RU2629116C2 (ru) | 2011-10-14 | 2017-08-24 | Эррэй Биофарма Инк. | Полиморфы arry-380, селективного ингибитора erbb2, и фармацевтические составы, содержащие их |
| CN105153046A (zh) * | 2015-08-25 | 2015-12-16 | 佛山市赛维斯医药科技有限公司 | 双卤素取代的乙氧基苯并喹唑啉类酪氨酸激酶抑制剂及用途 |
| CN105153047A (zh) * | 2015-08-25 | 2015-12-16 | 佛山市赛维斯医药科技有限公司 | 含新型苯并喹唑啉和邻位氟结构的酪氨酸激酶抑制剂及用途 |
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| WO2020262998A1 (ko) * | 2019-06-26 | 2020-12-30 | 한미약품 주식회사 | 항 종양 활성을 갖는 신규 퀴나졸린 유도체 및 이를 포함하는 약학 조성물 |
| WO2021231400A1 (en) * | 2020-05-12 | 2021-11-18 | Accutar Biotechnology, Inc. | Bis-aryl ethers containing n-acyl azetidine as egfr/her2 inhibitors |
| WO2022105908A1 (zh) * | 2020-11-23 | 2022-05-27 | 上海和誉生物医药科技有限公司 | Egfr抑制剂及其制备方法与在药学上的应用 |
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| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| JP2007500177A (ja) * | 2003-07-29 | 2007-01-11 | アストラゼネカ アクチボラグ | チロシンキナーゼ阻害剤としてのピペリジルキナゾリン誘導体 |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| DK1667991T3 (da) * | 2003-09-16 | 2008-08-18 | Astrazeneca Ab | Quinazolinderivater som tyrosinkinaseinhibitorer |
| US20070032513A1 (en) * | 2003-09-16 | 2007-02-08 | Hennequin Laurent F A | Quinazoline derivatives |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| CN1882570B (zh) * | 2003-09-19 | 2010-12-08 | 阿斯利康(瑞典)有限公司 | 喹唑啉衍生物 |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| MXPA06003341A (es) * | 2003-09-25 | 2006-06-08 | Astrazeneca Ab | Derivados de quinazolina. |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| ATE413389T1 (de) * | 2004-02-03 | 2008-11-15 | Astrazeneca Ab | Chinazolinderivate |
| US20070232607A1 (en) * | 2004-06-04 | 2007-10-04 | Bradbury Robert H | Quinazoline Derivatives as Erbb Receptor Tyrosine kinases |
-
2004
- 2004-09-14 JP JP2006526684A patent/JP2007505873A/ja active Pending
- 2004-09-14 CN CNA2004800335692A patent/CN1882573A/zh active Pending
- 2004-09-14 CA CA002539022A patent/CA2539022A1/en not_active Abandoned
- 2004-09-14 AU AU2004272350A patent/AU2004272350A1/en not_active Abandoned
- 2004-09-14 MX MXPA06002963A patent/MXPA06002963A/es unknown
- 2004-09-14 EP EP04768477A patent/EP1664028A1/en not_active Withdrawn
- 2004-09-14 US US10/571,851 patent/US20070032508A1/en not_active Abandoned
- 2004-09-14 BR BRPI0414447-3A patent/BRPI0414447A/pt not_active Application Discontinuation
- 2004-09-14 WO PCT/GB2004/003931 patent/WO2005026151A1/en not_active Ceased
-
2006
- 2006-03-12 IL IL174258A patent/IL174258A0/en unknown
- 2006-03-15 ZA ZA200602190A patent/ZA200602190B/en unknown
- 2006-03-23 NO NO20061321A patent/NO20061321L/no not_active Application Discontinuation
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